2-Bromopyridine → 4-(2-Pyridyl)Benzoic Acid

Participants

Reaction Conditions

Reaction Steps

To a suspension of 4-carboxybenzeneboronic acid (0.660 g, 3.98 mmol) and 2-bromopyridine (0.38 mL, 3.98 mmol) in dry acetonitrile (20 mL) was added 0.4 M aqueous sodium carbonate (20 mL) and mixture purged with nitrogen for 10 minutes. Tetrakis(triphenylphosphine)palladium(0) (0.240 g) was then added and the reaction mixture heated to 90° C. for 20 hours. The hot mixture was filtered through celite and concentrated in vacuo to remove acetonitrile. The resulting aqueous suspension was diluted with water (20 mL), washed with dichloromethane (2×40 mL), and then acidified to pH 6 by the addition of concentrated hydrochloric acid. The resulting white suspension was diluted with water (20 mL), filtered and the solid product dried in vacuo at 50° C. overnight to give the title compound (0.662 g, 84%) as a white solid, m.p. 232-234° C.

Provenance & Evidence